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A Pharmaceutical Composition Comprising a Menthane Carboxylic Acid Amide

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A Pharmaceutical Composition Comprising a Menthane Carboxylic Acid Amide (19) TZZ ¥Z Z_T (11) EP 2 730 280 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 14.05.2014 Bulletin 2014/20 A61K 31/196 (2006.01) A61K 45/06 (2006.01) A61P 11/00 (2006.01) A61P 17/00 (2006.01) (2006.01) (2006.01) (21) Application number: 12191877.5 A61K 9/00 A61Q 11/00 (22) Date of filing: 08.11.2012 (84) Designated Contracting States: • Siegel, Sven AL AT BE BG CH CY CZ DE DK EE ES FI FR GB 37671 Höxter (DE) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Middendorf, Silke PL PT RO RS SE SI SK SM TR 49196 Bad Laer (DE) Designated Extension States: BA ME (74) Representative: Fabry, Bernd IP2 Patentanwalts GmbH (71) Applicant: Symrise AG Schlossstrasse 523 37603 Holzminden (DE) 41238 Mönchengladbach (DE) (72) Inventors: • Krammer, Gerhard 37603 Holzminden (DE) (54) A pharmaceutical composition comprising a menthane carboxylic acid amide (57) Suggested is a pharmaceutical composition, phenyl)-amide. comprising menthane carboxylic acid-N-(4-methoxy- EP 2 730 280 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 730 280 A1 Description Field of invention 5 [0001] The present invention belongs to the area of anti-inflammatory compositions and refers to a specific menthane carboxylic acid amide as a pharmaceutical composition and also oral compositions comprising said amide. State of the art 10 [0002] Inflammation represents a part of the complex biological response of vascular tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. An inflammation is different to a mere irritation like goose bumps or itching in the case of the skin. Inflammation is a protective attempt by the organism to remove the injurious stimuli and to initiate the healing process. Inflammation is not a synonym for infection, even in cases where inflammation is caused by infection. Although infection is caused by a microorganism, inflammation is one of the responses of the organism to the pathogen. 15 However, inflammation is a stereotyped response, and therefore it is considered as a mechanism of innate immunity, as compared to adaptive immunity, which is specific for each pathogen. An acute inflammation is preferably characterized by clinical signs: pain, redness, immobility (loss of function), swelling and/or heat. A very typical embodiment of inflam- mation is acne vulgaris. [0003] The process of acute inflammation is initiated by cells already present in all tissues. These cells have on their 20 surfaces certain pattern recognition receptors (PRRs), which recognize molecules that are broadly shared by pathogens but distinguishable from host molecules (pathogen-associated molecular patterns (PAMPs)). At the onset of an infection, burn, or other injuries, these cells undergo activation (as one of their PRRs recognizes a PAMP) and release inflammatory mediators (factors) responsible for the clinical signs of inflammation. Vasodilation and its resulting increased blood flow cause the redness ( rubor) and increased heat ( calor). Increased permeability of the blood vessels results in an exudation 25 (leakage) of plasma proteins and fluid into the tissue (edema), which manifests as swelling ( tumor). Some of the released mediators increase the sensitivity to pain dolor( ). The mediator molecules also alter the blood vessels to permit the migration of leukocytes, mainly neutrophils, outside of the blood vessels (extravasation) into the tissue. The neutrophils migrate along a chemotactic gradient created by the local cells to reach the site of injury. The loss of function (functio laesa)is probably the result ofa neurologicalreflex in responseto pain. Preferably,in thesense of thistext, an inflammation 30 is accompanied by an elevated level of inflammatory mediators (factors) like TNF-α (Tumor necrosis factor-alpha), interleukins, (preferably of IL-1, IL-6, IL-7, IL-8, IL-10, IL-13, IL-17, IL-18 and/or IL-31, in particular IL-1), prostaglandin (preferably PGl2, PGE2 and/or PGF2α), Interferon-gamma (INF-γ) and/or NF-κB (nuclear factor kappa-light-chain-en- hancer of activated B cells). [0004] Among the various types of inflammatories inflammation of the respiratory tract is one of the most common, 35 particular in winter time. The respiratory tract is divided into three segments: the upper respiratory tract, which includes the nose and nasal passages, paranasal sinuses, and throat or pharynx; the respiratory airways, which include the voice box or larynx, trachea, bronchi, and bronchioles; and the lungs, which include the respiratory bronchioles, alveolar ducts, alveolar sacs, and alveoli. The term upper respiratory infections, commonly referred to as URls, are used to refer to an acute infection that involves the upper respiratory tract, e.g., the nose, sinuses, pharynx or larynx. Acute upper respiratory 40 tract infections include rhinosinusitis (common cold), sinusitis, pharyngitis/tons illitis, laryngitis and sometimes bronchitis. Symptoms of URls commonly include congestion, cough, running nose, sore throat, fever, facial pressure and sneezing. These infections very often have inflammation as a symptom. An also very common infection is pharyngitis. Pharyngitis is, in most cases, a painful inflammation of the pharynx, and is colloquially referred to as a sore throat. Infection of the tonsils, i.e., tonsillitis, may occur simultaneously. About 90% of cases are caused by viral infection, with the remainder 45 caused by bacterial infection and, in rare cases, oral thrush (fungal candidiasis, e.g., in babies). Some cases of pharyngitis are caused by irritation from environmental irritants such as pollutants or chemical substances [0005] As a matter of fact countless actives are known from the state of the art. For example, US 4,136,163describe compounds having a physiological cooling effect on the skin and on the mucous membranes of the body, particularly those of the mouth, nose, throat and gastrointestinal tract. These compounds are 3-substituted-p-menthanes of formula 50 (I): 55 2 EP 2 730 280 A1 5 10 [0006] Where R’, when taken separately, is hydrogen or an aliphatic radical containing up to 25 carbon atoms; R", 15 when taken separately is hydroxy, or an aliphatic radical containing up to 25 carbon atoms, with the proviso that when R’ is hydrogen R" may also be an aryl radical of up to 10 carbon atoms and selected from the group consisting of substituted phenyl, phenalkyl or substituted phenalkyl, naphthyl and substituted naphthyl, pyridyl (with typical values being benzyl, naphthyl, 4-methoxyphenyl, 4-hydroxyphenyl, 4-methylphenyl, 3-hydroxy-4-methylphenyl, 4-fluorophenyl, 4-nitrophenyl, 2-hydroxynaphthyl, pyridyl, etc.); and ’R’ and R", when taken together with the nitrogen atom to which 20 they are attached, represent a cyclic or heterocyclic group of up to 25 carbon atom. [0007] US4,136,163 teaches that the compounds of formula (I) are suitable for a wide variety of applications including edible and potable compositions, toiletries, medicaments including counter-irritants, cough mixtures and throat lozenges as well as miscellaneous compositions such as water soluble adhesive compositions for envelopes, stamps, adhesive labels etc. Regarding medicaments, US 4,136,163 teaches that because of their cooling effect on the skin and on the 25 mucous membranes of the mouth, throat and nose and of the gastrointestinal tract the 3-substituted-p-menthanes may be used in a variety of oral medicines, nasal and throat sprays, and topical compositions. A particular utility is in the formulation of antacid and indigestion remedies. An anti-inflammatory effect of the compounds of formula (I) is not disclosed. [0008] More than fifty compounds of formula (I) are specifically mentioned in US4,136,163. Although menthane car- 30 boxylic acid-N-(4-methoxyphenyl)-amide is one of the compounds explicitly mentioned, no example of a composition comprising said compound is provided. Indeed, none of the twenty-four given composition examples comprises any compound of formula (I) wherein R’ is hydrogen and R" is an aryl radical of up to 10 carbon atoms as defined above. [0009] WO2009 021558A1relates to products and mixtures comprising (a) pellitorin and (b) selected cooling agents different from menthane carboxylic acid-N-(4-methoxyphenyl)-amide, and the use of such mixtures for soothing irritated 35 oral and/or nasal tissues and for reducing bitterness. The mixture optionally comprises one or more additional physio- logical cooling agents selected from the group consisting of N-substituted-p-menthane-3-carboxamides (as described in US 4,136,163), acyclic tertiary and secondary carboxamides, 3-(I-menthoxy)propan-1,2-diol, monomenthyl glutarate, monomenthyl succinate and its salts. The sole specific example of an N-substituted-p-menthane-3-carboxamide given in the document is ethyl-p-menthane-3-carboxamide. An anti-inflammatory effect of N-substituted-p-menthane-3-car- 40 boxamides is not disclosed. [0010] US6,231,900B1discloses a pastille confectionery product, suitable for the relief of cough and cold symptoms, comprising a coolant composition and a flavour composition each composition being in separate, distinct and discrete regions of the product, the coolant and flavour compositions being adapted to provide different release profiles; wherein the coolant composition is free of flavouring agents and the flavour composition is essentially free of cooling agents. 45 Anti-irritant or anti-inflammatory effects are not mentioned. [0011] US2009/0238905A1relates to a composition for reducing inflammation and irritation of endodermal tissue, such as that in the gastrointestinal tract and the respiratory tract. The formulation comprises an ingestible carrier or coating and an active mixture that includes bisabolol or extracts containing bisabolol and a ginger composition. The composition advantageously comprises one or more cooling agents, among others the above-mentioned menthyl-3-carboxylic acid 50 N-ethylamide. No further cooling agents of formula (I) are mentioned in US 2009/0238905. The ratio of bisabolol to the ginger composition in the active mixture is such that an irritation reducing action, an inflammation reducing action, or both, of the bisabolol and the ginger composition is increased synergistically.
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